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Showing Compound Limonin (FDB014715)

Record Information
Version1.0
Creation date2010-04-08 22:11:26 UTC
Update date2019-11-26 03:10:39 UTC
Primary IDFDB014715
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLimonin
DescriptionLimonin belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Based on a literature review a significant number of articles have been published on Limonin.
CAS Number1180-71-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP3.47ALOGPS
logP2.46ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)17.61ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area104.57 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity114.72 m³·mol⁻¹ChemAxon
Polarizability47.86 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC26H30O8
IUPAC name19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione
InChI IdentifierInChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3
InChI KeyKBDSLGBFQAGHBE-UHFFFAOYSA-N
Isomeric SMILESCC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1
Average Molecular Weight470.5116
Monoisotopic Molecular Weight470.194067936
Classification
Description Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid skeleton
  • Steroid lactone
  • 11-oxosteroid
  • Oxosteroid
  • 2-oxosteroid
  • Steroid
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Dioxepane
  • 1,4-dioxepane
  • Delta_valerolactone
  • Pyran
  • Oxane
  • Dicarboxylic acid or derivatives
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Furan
  • Carboxylic acid ester
  • Lactone
  • Ketone
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Dialkyl ether
  • Oxirane
  • Ether
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLimonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-7091800000-d189c180a34aeb636eb4Spectrum
Predicted GC-MSLimonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000900000-a4ab208d1fffee15d3df2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imr-0012900000-ed371143180c1aea6bc72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9120100000-66524d5b327a652ced012017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0000900000-75a3d9f8a0f1fae147502017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0g2c-1002900000-4048ea92e5c743c331ac2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-4009200000-94a0f7fc00188c6b3e352017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d297686d7426b68c96ce2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-ff496abcb051f215a95e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0001900000-52252c8a0c93946623bb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-b8ab25ad98350c2823ca2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-0010900000-f78ec9bfcbf614a341cb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03gi-1460900000-329d430a9185fb234de42021-09-24View Spectrum
NMRNot Available
ChemSpider ID205258
ChEMBL IDNot Available
KEGG Compound IDC03514
Pubchem Compound ID235284
Pubchem Substance IDNot Available
ChEBI ID16226
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35921
CRC / DFC (Dictionary of Food Compounds) IDJVF49-D:JVF49-D
EAFUS IDNot Available
Dr. Duke IDLIMONIN
BIGG IDNot Available
KNApSAcK IDC00003719
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLimonin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
GrapefruitExpected but not quantifiedNot AvailablePHYTOHUB
LemonExpected but not quantifiedNot AvailableDUKE
Mandarin orange (Clementine, Tangerine)Expected but not quantifiedNot AvailableDUKE
Sour orangeExpected but not quantifiedNot AvailablePHYTOHUB
Sweet orangeExpected but not quantifiedNot AvailableDUKE, PHYTOHUB
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Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).